Photographic developer



Patented Apr. 12, 1932 UNITED STATES PATENT OFFICE GUSTAV BEDDELIEN' AND WERNER MULLER, OF LEIPZIG, GERMANY, ASSIGNOBS 'IO .LGFL .L'N'BCO OOBPOBA'IION, OI BINGHAMTON, NEW YORK, A CORPORATION O! m YORK Io Drawing. Application filed July 16, 1980, Serial No. 468,451, and in Germany August 19, 1989.

Our present invention relates to a process of developing photographic materials and new photographic developers.

It is based on the observation that with the 6 exception of the compounds which are twice h droxyethylated at each nitrogen atom, the N hydroxyethyl derivatives of 2.4-diamino-1- hydroxybenzene or of N-mono-acyl-2A-diamino-l-hydroxybenzene or of the nucleal 1 substitution products of these compounds are well suited as photographic developers in so far as they contain no nitro groups.

The compounds in question correspond to the general formula a v m, as, 3 3 meaning hydrogen, acyl, hydroxyethyl, at least one of these substituents being the hydroxyethyl, residue and at least one meaning hydrogen.

The sai compounds are very stable in solid and in dissolved condition are markably soluble and have the particular prop erty of developing the latent photographle image in a silver halide emulsion without formation of fog, even in solutions free from potassium bromide.

The following examples illustrate suitable compositions for photographic developers in accordance with our invention:

Example 1 6. 5 grams of the sulfate of 4-hydroxyethylamino-2- acetamino-I-h droxybenzene, 45 grams of crysta ized sodium suliite, and 1 grams of potassium carbonate are dissolved in grams of water. The developer has properties similar to those of the developer made from -hydroxyethylamino-l-hydroxybenzene.

Example 2 gram of the hydrochloride of 2-hydroxyethylamino- 4-acetamiuo-1-hydroxybenzene,

grams of crystallized sodium sulflte. and

grams of potassium carbonate are dissolved in grams of water.

The developer is of a similar activity but in a steeper gradation, than that of the developer made in accordance w1th our U. S. Patent 1,758,762.

Example 3 5 grams 0! the sulfate of 4-hydroxyethylamino2- amino-l-hydroxybenzene,

45 grams of crystallized sodium sulflte, and

0, 1 gram of potassium bromide are dissolved in 1000 grams of water.

This developer is similar in action to the 2.4-diamino-l-hydroxybenzene.

Example 4 1. 85 grams of the sulfate of 2-hydroxyethylamino-4- amino-l-hydroxybenzene, 10 grams or crystallized sodium sulflte, and 55 0. 2 grams of potassium bromide are dissolved in 200 grams or water.

E'aample 5 1. 5 grams of the sulfate of 4-di-[hydroxyethyl1-amino- 2-amino-1-h droxybenzene 10 grams 0! or s ilized sodium sulflte, and

0, 4 gram oi po ssium bromide are dissolved in 200 grams of water.

This developer is similar in action to that made from 2.4-diamino-1-hydroxybenzene.

Example 6 1 gram of the sulfate 0! 2-di-[hydroxyethyl]-amino- 4-amiuo-1-hydroxybenzene and 20 grams of crystallized sodiumsulflte are dissolved in 200 grams of water.

The developer is similar in action to a developer contalnmg 4-am1no-1-hydroxybenzene 1n the usual d1lut1on.

Example '7 1. 5 grams oi. the sulfate of 2-di-[hydroxyethyl1-aminoi-amino-l-h droxybenzene and grams of cry llized sodium suliite, and

gram otfpotassium bromide are dissolved in grams 0 water.

w, w, y, 3 meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.

2. A photographic developer containing together with other developer ingredients a compound of the general formula:

H-NOH:CH:OH a: and y meaning H, acyl, hydroxyethyl.

3. A photographic developer containing together with other developer ingredients a compound of the general formula:

H-NCH:CH:OH a: meaning H, acyl, hydroxyethyl.

4. A photographic developer containing together with' other developer ingredients 2-acetylamino 4 hydroxy-ethylamino 1 hydroxybenzene. V

5. A photographic developer comprising an alkaline solution containing a compound of the general formula:

N 1 2 II N w, w, y, y' meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.

6. A photographic developer comprising an alkaline solution containing a compound of the general formula: on

IINCH:CH:0H a: and 3 meaning H, acyl, hydroxyethyl.

7 A photographic developer comprising an alkaline solution containing a compound of the general formula:

H-NCH:CH1OH a; meaning H, acyl, hydroxyethyl.

8. A photographic developer comprising 1 an alkaline solution containing 2-acetylamino4-hydroxyethylamino 1 hydroxybenzene.

9. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:

N I I I I m, m, y, y meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and'at least one meaning hydrogen.

10. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:

w and y meaning H, acyl, hydroxyethyl.

11. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:

OH x

- H- OH|CH|OH w meaning H, acyl, hydroxyethyl.

12. The process of developing photographic materials which comprises treating the same with a solution containing 2-acetylamino-4;-hydroxyethylamino- 1 hydroxybenzene.

13. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula:

f 1 N 0 2 5 a w, 41 ;,y, 3 meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.

14. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula:

HNOH:GH:0H w and y meaning H, acyl, hydroxyethyl.

15. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula:

H- CH:0H:OH :1: meaning H, acyl, hydroxyethyl.

16. The process of developing photographic materials which compriscs treating the same with an alkaline solution containing sodium sulfite and 2-acetylamino-4c-hydroxyethylamino-l-hydroxybenzenc.

In testimony whereof, we afiix our signatures.

GUSTAV REDDELIEN. WERNER MULLER. 

